Water → HCID 86710026, compound

HRID 1468263Notes

Reaction equation

HRID 1468263 reaction equation
[C:1]([C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13](O)=[O:14])[CH:10]=[CH:9][N:8]2[C:16]=1[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:37][NH2:38].O>C1COCC1>[C:1]([C:5]1[N:6]=[C:7]2[CH:12]=[C:11]([C:13]([NH:37][NH2:38])=[O:14])[CH:10]=[CH:9][N:8]2[C:16]=1[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 682631,1'-CarbonyldiimidazoleHCID 68939501HCID 68939501, compound

Product 1

HCID 86710026HCID 86710026, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-tert-Butyl-3-cyclohexylmethylimidazo[1,2-a]pyridine-7-carboxylic acid (500 mg, 1.59 mmol) was suspended in THF (5.0 mL), and the suspension was stirred at room temperature for 1 hour after adding carbonyldiimidazole (CDI) (280 mg, 1.73 mmol). The reaction mixture was stirred at room temperature for 1 hour after adding hydrazine monohydrate (0.240 mL, 4.80 mmol). Water was added to the reaction mixture. The precipitated solid was collected by filteration, and dried under reduced pressure to give 2-tert-butyl-3-cyclohexylmethylimidazo[1,2-a]pyridine-7-carbohydrazide (331 mg, yield 79%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. customThe precipitated solid was collected by filteration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-ac5737b9578a4f5da680f3442d5ae30e
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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